Ethyl Acetate → N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide

HRID 432966ノート

反応式

HRID 432966 の反応式
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)(=[O:5])=[O:4].C(OCC)(=O)C>C(O)(=O)C.[Fe]>[NH2:14][C:9]1[CH:8]=[C:7]([NH:6][S:3]([CH2:2][Cl:1])(=[O:4])=[O:5])[CH:12]=[CH:11][C:10]=1[F:13]

参加物

5

反応物 2

HCID 8857Ethyl AcetateHCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

生成物 1

HCID 18760845N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide収率 94%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒2 回

反応条件

温度
80 °C

実験手順

A mixture of 12.5 g of iron powder (223 mmol) and 16 mL of an aqueous solution of acetic acid (8%) was heated to 80° C., and a solution of 6 g of I -chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide (22.3 mmol) in 20 mL of glacial acetic acid and 22 mL ethyl acetate was added dropwise to the mixture. After heating for 1.5 h the reaction mixture was filtered through a pad of Celite® and washed with 200 mL of ethyl acetate and water (twice with 25 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated under reduced pressure to yield 5 g (94%) of the title compound as a solid melting at 128-129° C.

後処理

  1. temperatureAfter heating for 1.5 h the reaction mixture
  2. filtrationwas filtered through a pad of Celite®
  3. washwashed with 200 mL of ethyl acetate and water (twice with 25 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bef168359c1344ba9cf349bd425414a3
出典データセット
uspto-grants-2003_12
特許番号
US06664400B2

反応ノート

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